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15 protocols using triethylamine et3n

1

Metal-Organic Complexation and Biomolecular Interactions

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All reagents and
solvents used in this synthesis were commercially available. Reagent-grade
chemicals were used in this experiment. Hence, no further purification
was needed. Salicylaldehyde, 5-bromo Salicylaldehyde, 4-bromo aniline,
ctDNA, HSA, EB, and DAPI were obtained from Sigma-Aldrich Chemicals.
CuCl2, ZnCl2, and triethyl amine (Et3N) were purchased from Merck. Elemental analyses were performed using
a PerkinElmer 240C elemental analyzer. Electronic absorption spectral
data were collected by using a PerkinElmer UV–vis Lambda 365
spectrophotometer at room temperature. The concentration of ctDNA
per nucleotide was determined by absorption spectroscopy using a molar
extinction coefficient (€) 6600 (M–1 cm–1) at 260 nm. ctDNA interaction studies were performed
in a citrate-phosphate (CP) buffer of 10 mM [Na+] at pH
7.40 containing 0.5 mM Na2HPO4, and HSA interaction
studies were performed in Tris buffer.
Caution! Mercury salts are extremely toxic, so proper caution should be taken
before use.
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2

Functionalized Hybrid Nanoparticle Synthesis

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Safranin O (≥85%), sodium ascorbate (99%), tetraethyl orthosilicate (TEOS, 98%), lithium bis(trimethylsilyl)amide (LiN(SiMe3)2, 97%), phosphorous trichloride (PCl3, 99%), dichlorotriphenylphosphorane (Ph3PCl2, 95%), were purchased from Sigma Aldrich. Cetyltrimethylammonium bromide (CTAB, >99%) was purchased from VWR. Triethylamine (Et3N) from Merck was distilled and dried over molecular sieves (3 Å). Sodium hydroxide (98%) and copper(ii) sulfate pentahydrate (98.5%) were purchased from J. T. Barker. 3-Azidopropyl triethoxysilane (97%), camptothecin (>98%) and 2-propynylamine (97%) were purchased from fluorochem. Polyetheramine copolymer (PEO-PPO-NH2), sold under trade name Jeffamine® M-2005, with nominal molecular weight of 2000 g mol−1, was purchased from Huntsman Performance Products. Deuterated chloroform (CDCl3), (99.8%, Sigma Aldrich) was used for NMR measurements. Uranyless EM Stain (contrast stain solution for TEM) was purchased from EMS. Solvents were purchased from VWR and Alfa Aesar, and used as received if not stated otherwise. Anti-LAMP1 rabbit primary antibody and goat anti-rabbit secondary antibody IgG H&L (Alexa Fluor® 488) were purchased from Abcam. DAPI was purchased from Sigma-Aldrich.
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3

Synthesis and Characterization of Lipid-Based Nanoparticles

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3- aminopyrazole, 4- dimethylaminopyridine (DMAP), 5- bromovanillin, dimethyl sulfoxide (DMSO), dimethylformamide (DMF), ethanol (EtOH), methanol (MeOH), methylene chloride (CH2Cl2), MTT reagent, phosphate buffered saline (PBS), podophyllotoxin (P), tetronic acid, and triethylamine (Et3N) were purchased from Sigma-Aldrich or Fisher Scientific (Milwaukee, WI/Fairlawn,NJ). Chloroform solutions of 1,2-dipalmitoyl-sn-glycero-3-phophate (monosodium salt) (DPPA); 1,2-dipalmitoly-snglycero-3-phosphocholine (DPPC); 1,2-distearoyl-sn-glycerol-3-phosphoethanolamin-N-[methoxy(polyethylene glycol) -2000] ammonium salt (DSPE-PEG2000); and 1,2-distearoyl-sn-glycero-3-phospho-ethanolamine-N-(polyethyleneglycol)-5000) (ammonium salt) (DSPE-PEG5000) were purchased from Avanti Polar Lipids (Alabaster, AL). COATSOME® FE-6060GL (DPPE-Glu) was purchased from NOF America Corporation.
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4

Multifunctional Polymeric Biomaterials

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1,4-Butanediol diacrylate (BDA) (90%, Sigma
Aldrich), 5-amino-1-pentanol (AP) (95%, Sigma Aldrich), 5-norbornene-2-methylamine
(mixture of isomers, TCL), d-(+)-glucosamine hydrochloride
(Sigma Aldrich), methacryloyl chloride (97%, Sigma Aldrich, contains
200 ppm monomethyl ether hydroquinone as a stabilizer), potassium
carbonate (Alfa Aesar),HEMA (Sigma Aldrich), 4-cyano-4-[(dodecylsulfanylthiocarbonyl)sulfanyl]pentanoic
acid (97%, HPLC, Sigma Aldrich), azobisisobutyronitrile (AIBN) (98%,
Sigma Aldrich), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDC) (Sigma Aldrich), N-hydroxysuccinimide (NHS) (Merck), triethyl amine (Et3N) (Sigma Aldrich), and all other chemicals were of analytical
grade, obtained from commercial suppliers, and used without further
purification unless otherwise specified. Tetrazine amine (Tz-NH2) was synthesized according to our previous study.58 (link)
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5

Flame-Retardant Textile Modification

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The experiments were carried out using a commercial cotton woven fabric (twill 3/1, 230 g/m2, white, CHT R. Beitlich GmbH, Tübingen, Germany), a commercial 50/50 CO/PET woven fabric (warp sateen 4/1, 340 g/m2, orange, Huntsman Textile Effects GmbH, Langweid am Lech, Germany (PET/CO1)), a commercial 50/50 CO/PET core yarn fabric (twill 2/1, core PET, CO shell, 170 g/m2, camouflage, Bluecher GmbH, Erkrath, Bluecher GmbH, Germany d(PET/CO1)), and a 50/50 COPA core yarn fabric (twill 2/1, core PA, CO shell, 190 g/m2, camouflage, Bluecher GmbH, Erkrath, Germany). Hexachlorotriphosphazene was obtained from Eurolabs Limited (Crawley, UK) and allyl amine (≥99%) from Merck (Germany). Tetrahydrofuran (THF, ≥99.9%) were obtained from Carl Roth (Karlsruhe, Germany). Triethylamine (Et3N, ≥99%), was obtained from Sigma-Aldrich (St. Louis, USA). All solvents were dried before use.
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6

Folic Acid-Conjugated Gold Nanoparticles for Cancer Therapy

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Tetrachloroauric acid trihydrate (HAuCl4·3H2O), tetraoctylammonium bromide (TOAB), lipoic acid (LA), folic acid (FA), sodium borohydride (NaBH4), N-hydroxysuccinimide (NHS), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC), ethylenediamine (NH2)2(CH2)2, t-butyloxycarbonyl anhydride (Boc2O), dimethylsulfoxide (DMSO), N,N′-dicyclohexylcarbodiimide (DCC), triethylamine (Et3N), N-disuccinimydyl carbonate, N,N-diisopropylethylamine (DIPEA), doxorubicin (Dox) were purchased from Sigma Aldrich and used without further purification.
Tetrahydrofuran (THF), dimethylformamide (DMF), dichloromethane (DCM), diethyl ether (Et2O), ethyl acetate (EtOAc), chloroform (CHCl3), sodium carbonate (Na2CO3), anhydrous magnesium sulfate (MgSO4), acetone and any other solvents were obtained from Avantor, Poland. All glassware was carefully cleaned with an acidic solution of KMnO4 (overnight), piranha solution (H2SO4 : H2O2 : H2O, 1 : 1 : 3) (2 h), rinsed with large amounts of Milli-Q water and dried.
EMEM media was a product of the American Type Tissue Culture Collection (ATCC, Rockville, MD). RPMI-1640 without folic acid was purchased from Thermo Fisher Scientific (USA). 3-(4,5-Dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) were obtained from Sigma Aldrich. Fetal calf serum was a product of Biological Industries (Israel).
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7

Preparation and Characterization of PLGA Nanoparticles

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PLGA (75:25, molecular weight 66,000–107,000 Da), acetone, 3-[4,5-dimethylthiazol-2-yl]-3,5-diphenyltetrazolium bromide salt (used for MTT tests), dimethylformamide (DMF), phosphate-buffered saline (PBS) tablets, dimethyl sulfoxide (DMSO), methanol (CH3OH), methylene chloride (CH2Cl2), petroleum ether, 4-phenylbenzoic acid, tetrahydrofuran (THF), triethylamine (Et3N) and amphotericin B solution (250 μg/mL) were all purchased from Sigma Aldrich (Milan, Italy). Oxalyl chloride [(CO)2Cl2] was purchased from Alpha Aesar (Ward Hill, MA, USA). Dry THF was distilled over sodium and benzophenone. Dry DMF, CH2Cl2, and Et3N were used as supplied. Petroleum ether refers to alkanes with a boiling point 40–60 °C. Poloxamer 188 was obtained from BASF (Ludwigshafen, Germany). Human keratinocyte (NCTC-2544) and chondrocyte (C-28) cells were provided by the Istituto Zooprofilattico Sperimentale della Lombardia e dell’Emilia Romagna. Dulbecco’s Modified Eagle Medium (DMEM) supplemented with glutamax I, penicillin/streptomycin solution, fetal bovine serum (FBS) and trypsin/ethylene diamine tetraacetic acid (EDTA) were all purchased from GIBCO (Life Technologies, Monza, Italy).
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8

Synthesis and Characterization of 4-Fluoro-3-Nitroaniline Derivative

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The reagents 4-fluro-3-nitroaniline, triethylamine (Et3N), acetic anhydride, chloroacetyl chloride, chloroform, and ethanol were purchased from Merck/Sigma-Aldrich® (Darmstadt, Germany). The recrystallization technique was used to purify the compound and its purity was confirmed from the melting point measurement using the MQAPF-302 (Microquímica, São Paulo, Brazil) apparatus. A Shimadzu spectrometer model IRPrestige-21 FT-IR (Barueri, São Paulo, Brazil) with an attenuated total reflection (ATR) accessory produced the infrared (IR) spectrum. The hydrogen and carbon nuclear magnetic resonance (NMR) spectra were obtained from a Bruker Avance 400 apparatus. The hydrogen spectra (1H) were obtained at the frequency of 400 and 500 MHz using deuterated solvents chloroform (CDCl3) and dimethylsulfoxide (DMSO). The carbon spectra (13C) were obtained at the frequency of 101 and 126 MHz using deuterated solvents chloroform (CDCl3) and dimethylsulfoxide (DMSO). The chemical distances (δ) were generated in parts per million (ppm) and in Hertz (Hz) the coupling constants (J) were determined.
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9

Functionalization of Silicon Surfaces

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N-type phosphorus-doped silicon (111) wafers,
with resistivity of 0.01–0.018 Ω·cm, were used in
these experiments. Heptadecafluoro-1,1,2,2-tetrahydrodecyl) dimethylchlorosilane
(95% purum), (heptadecafluoro-1,1,2,2-tetrahydrodecyl)methyldichlorosilane
(97% purum) and 1H,1H,2H,2H-perfluorodecyltrichlorosilane (97% purum, stabilized
with copper) were purchased from abcr GmbH. Chloro-decyl-dimethylsilane,
acetone, diethyl ether, CH2Cl2 and triethylamine
(Et3N) were purchased from Sigma-Aldrich. For surface modification,
CH2Cl2 was dried in a PureSolv EN solvent purification
system (Innovative Technology). Deionized (DI) water was obtained
from a Milli-Q Integral water purification system (Merck-Millipore).
Phosphate buffered saline (PBS, 10 mM, pH 7.4) was prepared from a
solution of NaCl (8.01 g/L), Na2HPO4 (1.41 g/L),
KH2PO4 (0.27 g/L) and KCl (0.20 g/L) in DI water.
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10

Palladium-Catalyzed Reaction Optimization

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Solvents (ethyl levulinate, methyl levulinate, 2-MeTHF, and dichloromethane), substrates (119), nucleophiles (ah), and triethylamine (Et3N) were purchased from Sigma-Aldrich (St. Louis, MO, USA), and they were used without any further purification. The Pd(OAc)2 and the ligands (PPh3 and XantPhos) were also purchased from Sigma-Aldrich. TLC plates (silica gel on TLC Al foils with fluorescence indicators of 254 nm) and the silica gel (high-purity grade, average pore size 60 Å (52–73 Å), 70–230 mesh) were purchased from Sigma-Aldrich (St. Louis, MO, USA).
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